Document Detail


Reaction of bromomethylazoles and tosylmethyl isocyanide. A novel heterocyclization method for the synthesis of the core of marine alkaloids variolins and related azolopyrimidines.
MedLine Citation:
PMID:  15255724     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A novel and efficient synthesis of the pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine system, the heterocyclic core of the variolin family of marine alkaloids, is described. The route involves the reaction of 3-bromo-2-(bromomethyl)pyrrolo[2,3-b]pyridine and tosylmethyl isocyanide (TosMIC) under phase-transfer conditions. This unprecedented reaction was also used to synthesize a series of new methoxycarbonyl azolopyrimidines by reaction of TosMIC with bromomethylindoles, bromomethylbenzimidazole, and bromomethylpyrazole. Hydrolysis and decarboxylation of 5-bromo-7-methoxycarbonylpyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine obtained by this heterocyclization process and installation of the pyrimidine moiety in the C5 position open an alternative approach to complete a total synthesis of variolin B.
Authors:
Javier Mendiola; Alejandro Baeza; Julio Alvarez-Builla; Juan J Vaquero
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Jul 
Date Detail:
Created Date:  2004-07-16     Completed Date:  2004-09-17     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4974-83     Citation Subset:  IM    
Affiliation:
Departamento de Química Orgánica, Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, Spain.
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MeSH Terms
Descriptor/Qualifier:
Alkaloids / chemical synthesis*,  chemistry
Animals
Azoles / chemistry*
Cyanides / chemistry*
Cyclization
Molecular Structure
Porifera / chemistry
Pyrimidines / chemical synthesis*,  chemistry
Tosyl Compounds / chemistry*
Chemical
Reg. No./Substance:
0/Alkaloids; 0/Azoles; 0/Cyanides; 0/Pyrimidines; 0/Tosyl Compounds

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